Development of treatment agents against ulcerative colitis from medicinal flowers

• Project/Area Number: 26460135
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Natural medicines
• Research Institution: Kyoto Pharmaceutical University
• Principal Investigator: Nakamura Seikou 京都薬科大学, 薬学部, 准教授 (20411035)
• Co-Investigator(Kenkyū-buntansha): 松田 久司 京都薬科大学, 薬学部, 教授 (40288593)
• Project Period (FY): 2014-04-01 – 2017-03-31
• Project Status: Completed (Fiscal Year 2016)
• Budget Amount: ¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000); Fiscal Year 2016: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000); Fiscal Year 2015: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000); Fiscal Year 2014: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
• Keywords: メディシナルフラワー / 潰瘍性大腸炎 / 好中球 / 脱顆粒抑制作用 / 一酸化窒素産生抑制作用 / キンモクセイ花部 / トリテルペン / カフェ酸誘導体 / 構造活性相関 / トリテルペン誘導体 / 桂皮酸誘導体 / アシル化フラボノール配糖体 / 金針花 / イランイランノキ花部

Outline of Final Research Achievements

We have researched effective compounds against ulcerative colitis from medicinal flowers. As the research results, over 150 constituents were isolated from the flowers of Osmanthus fragrans var. aurantiacus, Camellia sasanqua, Camellia sinensis var. assamica, daylily (Hemerocallis fulva var. kwanso, H. flava, H. minor), Paeonia suffruticosa, Paeonia lactiflora, Dendrobium pharaenopsis. Among them, triterpenes and caffeic acid derivatives significantly showed show the anti-degranulation effects from neutorophil-like cells and the inhibitory effects on NO production, and the information about their structure-activity relationships were obtained. In addition, we could clarify a part of the mechanism of actions of the triterpenes.

Research Products

• [Journal Article] Structure of a coumaric acid analogue with a monoterpene moiety from the flowers of Osmanthus fragrans var. aurantiacus and evaluation of cinnamic acid analogues as Nitric Oxide production and degranulation inhibitors (2016)
  • Author(s): Seikou Nakamura, Jiang Liu, Souichi Nakashima, Keiko Ogawa, Takashi Ueda, Eri Onishi, Kiwako Kurooka, Yuko Moriwaki, Kaori Ryu, Bin Xu, Takahiro Matsumoto, Tomoe Ohta, Masashi Fukaya, Masayuki Yoshikawa, Hisashi Matsuda
  • Journal Title: Natural Product Communications Volume: 11 Pages: 1123-1128
  • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
• [Journal Article] New biofunctional effects of the flower buds of Camellia sinensis and its bioactive acylated oleanane-type triterpene oligoglycosides (2016)
  • Author(s): Hisashi Matsuda, Seikou Nakamura, Toshio Morikawa, Osamu Muraoka, Masayuki Yoshikawa
  • Journal Title: Journal of Natural Medicines Volume: 70 Issue: 4 Pages: 689-701
  • DOI: 10.1007/s11418-016-1021-1
  • Peer Reviewed
• [Journal Article] γ-Lactam alkaloids from the flower buds of daylily (2016)
  • Author(s): Takahiro Matsumoto, Seikou Nakamura, Souichi Nakashima, Tomoe Ohta, Mamiko Yano, Junichiro Tsujihata, Junko Tsukioka, Keiko Ogawa, Masashi Fukaya, Masayuki Yoshikawa, Hisashi Matsuda
  • Journal Title: Journal of Natural Medicines Volume: 70 Issue: 3 Pages: 376-383
  • DOI: 10.1007/s11418-015-0963-z
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] New potent accelerator of neurite outgrowth from Lawsonia inermis flower under non-fasting condition (2016)
  • Author(s): Yoshimi Oda, Souichi Nakashima, Seikou Nakamura, Mamiko Yano, Masanori Akiyama, Kayo Imai, Tomohito Kimura, Akiko Nakata, Miyuki Tani, Hisashi Matsuda
  • Journal Title: Journal of Natural Medicines Volume: 70 Issue: 3 Pages: 384-390
  • DOI: 10.1007/s11418-016-0974-4
  • Peer Reviewed
• [Journal Article] Inhibitors of melanogenesis in B16 melanoma 4A5 cells from flower buds of Lawsonia inermis (Henna) (2015)
  • Author(s): Souichi Nakashima, Yoshimi Oda, Seikou Nakamura, Jiang Liu,; Koko Onishi, Miki Kawabata, Hisako Miki, Yugo Himuro, Masayuki Yoshikawa, Hisashi Matsuda
  • Journal Title: Bioorganic & Medicinal Chemistry Letters Volume: 25 Issue: 13 Pages: 2702-2706
  • DOI: 10.1016/j.bmcl.2015.04.052
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Constituents of flowers of Paeoniaceae plants, Paeonia suffruticosa and Paeonia lactiflora (2015)
  • Author(s): Ogawa, Keiko; Nakamura, Seikou; Sugimoto, Sachiko; Tsukioka, Junko; Hinomaru, Fusako; Nakashima, Souichi; Matsumoto, Takahiro; Ohta, Tomoe; Fujimoto, Katsuyoshi; Yoshikawa, Masayuki
  • Journal Title: Phytochemistry Letters Volume: 12 Pages: 98-104
  • DOI: 10.1016/j.phytol.2015.03.002
  • Peer Reviewed / Open Access / Acknowledgement Compliant
• [Journal Article] Acylated oleanane-type triterpene oligoglycosides from the flower buds of Camellia sinensis var. assamica (2015)
  • Author(s): Tomoe Ohta, Seikou Nakamura, Souichi Nakashima, Takahiro Matsumoto, Keiko Ogawa, Katsuyoshi Fujimoto, Masashi Fukaya, Masayuki Yoshikawa, Hisashi Matsuda
  • Journal Title: Tetrahedron Volume: 71 Issue: 5 Pages: 846-851
  • DOI: 10.1016/j.tet.2014.12.049
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Chemical structures of constituents from the flowers of Osmanthus fragrans var. aurantiacus (2015)
  • Author(s): Jiang Liu, Seikou Nakamura, Bin Xu, Takahiro Matsumoto, Tomoe Ohta, Katsuyoshi Fujimoto, Keiko Ogawa, Masashi Fukaya, Shiori Miyake, Masayuki Yoshikawa, Hisashi Matsuda
  • Journal Title: Journal of Natural Medicines Volume: 69 Issue: 1 Pages: 135-141
  • DOI: 10.1007/s11418-014-0869-1
  • NAID: 40020305763
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] A Rare Glutamine Derivative from the Flower Buds of Daylily (2014)
  • Author(s): Takahiro Matsumoto, Seikou Nakamura, Tomoe Ohta, Katsuyoshi Fujimoto, Masayuki Yoshikawa, Keiko Ogawa, Hisashi Matsuda
  • Journal Title: Organic Letters Volume: 16 Issue: 11 Pages: 3076-3078
  • DOI: 10.1021/ol501182v
  • Peer Reviewed
• [Presentation] Cyanogenetic Glycosides from the Leaves and Stems of H.macrophylla and the Flowers of H.macrophylla var. thunbergii. (2016)
  • Author(s): Seikou Nakamura, Zhibin Wang, Souichi Nakashima, Masayuki Yoshikawa, Hisashi Matsuda
  • Organizer: International Symposium on Natural Products for the Future 2016 Tokushima
  • Place of Presentation: 徳島文理大学
  • Year and Date: 2016-09-03
  • Int'l Joint Research
• [Presentation] The search for new functionsof the flowers of Dendrobium phalaenopsis (2016)
  • Author(s): Yoshimi Oda, Souichi Nakashima, Seikou Nakamura, Hisashi Matsuda
  • Organizer: PROCEEDINGS OF THE 9th CSP-KSP-JSP JOINT SYMPOSIUM ON PHARMACOGNOSY & 2016 ANNUAL CONFERENCE OF COMMITTEE OF CHINESE TRADITIONAL AND NATURAL MEDICINES, CHINESE PHARMACEUTICAL ASSOCIATION
  • Place of Presentation: Shanghai University of Traditional Chinese Medicine, 上海
  • Year and Date: 2016-05-30
  • Int'l Joint Research
• [Presentation] メディシナルフラワー研究：キンモクセイ (Osmanthus fragrans var. aurantiacus) 花部を素材とした新規生体機能性を有する含有成分及びその誘導体の探索研究 (2016)
  • Author(s): 深谷 匡, 中村誠宏, 中嶋聡一, 小川慶子, 松本崇宏, 太田智絵, 劉 江, 松田久司
  • Organizer: 日本薬学会第136年会
  • Place of Presentation: 神奈川県横浜市 パシフィコ横浜
  • Year and Date: 2016-03-28
• [Presentation] メディシナルフラワー研究：中国産金針花含有アルカロイドの生体機能性 (2016)
  • Author(s): 奥田若奈, 松本崇宏, 中村誠宏, 中嶋聡一, 吉川雅之, 松田久司
  • Organizer: 日本薬学会第136年会
  • Place of Presentation: 神奈川県横浜市 パシフィコ横浜
  • Year and Date: 2016-03-28
• [Presentation] ボタン (Paeonia suffruticosa) 花部のコラーゲン生成促進作用 (2016)
  • Author(s): 砥上宏子, 森浦俊次, 中嶋聡一, 中村誠宏, 河村友惟, 冨永杏子, 吉川雅之, 松田久司
  • Organizer: 日本薬学会第136年会
  • Place of Presentation: 神奈川県横浜市 パシフィコ横浜
  • Year and Date: 2016-03-28
• [Presentation] ヘンナ (Lowsonia inermis) 花部の新規機能性探索研究 (2015)
  • Author(s): 中嶋聡一, 中尾悠里, 中村誠宏, 尾田好美, 松田久司
  • Organizer: 第33回メディシナルケミストリーシンポジウム
  • Place of Presentation: 千葉県千葉市 幕張国際研修センター
  • Year and Date: 2015-11-26
• [Presentation] STRUCTURE OF CONSTITUENTS ISOLATED FROM THE FLOWER BUDS OF CANANGA ODORATA AND THEIR BIOACTIVITIES (2015)
  • Author(s): Takahiro Matsumoto, Seikou Nakamura, Souichi Nakashima, Masayuki Yoshikawa, Hisashi Matsuda
  • Organizer: 7th Asian Association of Schools of Pharmacy (AASP) Conference
  • Place of Presentation: Taipei, Taiwan, GIS NTU CONVENTION CENTER
  • Year and Date: 2015-11-01
  • Int'l Joint Research
• [Presentation] RESEARCH OF BIOFUNCTIONAL CONSTITUENTS FROM ASSAM TEA FLOWER (2015)
  • Author(s): Tomoe Ohta, Seikou Nakamura, Souichi Nakashima, Masayuki Yoshikawa, Hisashi Matsuda
  • Organizer: 7th Asian Association of Schools of Pharmacy (AASP) Conference
  • Place of Presentation: Taipei, Taiwan, GIS NTU CONVENTION CENTER
  • Year and Date: 2015-11-01
  • Int'l Joint Research
• [Presentation] 桂皮酸誘導体の一酸化窒素産生抑制作用 (2015)
  • Author(s): 深谷 匡, 中村誠宏, 上田 昂, 中嶋聡一, 黒岡希和子, 平松慶子, 笠 香織, 小川慶子, 劉 江, 伊藤 謙, 吉川雅之, 松田久司
  • Organizer: 日本生薬学会第62回年会
  • Place of Presentation: 岐阜県岐阜市 長良川国際会議場
  • Year and Date: 2015-09-11
• [Presentation] New Triterpene Oligoglycosides from the Flower Buds of Camellia sinensis var. assamica (2015)
  • Author(s): Tomoe Ohta, Seikou Nakamura, Souichi Nakashima, Masayuki Yoshikawa, Hisashi Matsuda
  • Organizer: INAUGURAL SYMPOSIUM OF THE PHYTOCHEMICAL SOCIETY OF ASIA
  • Place of Presentation: 徳島県徳島市 徳島文理大学
  • Year and Date: 2015-08-30
  • Int'l Joint Research
• [Presentation] ラン科デンファレ (Dendrobium pharaenopsis) 花部の含有成分 (2015)
  • Author(s): 尾田好美，小川裕樹，中嶋聡一，中村誠宏，河端未来，秋山真範，木村智仁，前川友希，吉川雅之，松田久司
  • Organizer: 日本薬学会第135年会
  • Place of Presentation: 兵庫県神戸市 デザイン・クリエイティブセンター神戸
  • Year and Date: 2015-03-27
• [Presentation] メディシナルフラワー研究: ボタンおよびシャクヤク花部の抗酸化作用成分 (2015)
  • Author(s): 小川慶子，中村誠宏，杉本幸子，月岡淳子，日丸富紗子，中嶋聡一，松本崇宏，太田智絵，吉川雅之，松田久司
  • Organizer: 日本薬学会第135年会
  • Place of Presentation: 兵庫県神戸市 神戸学院大学
  • Year and Date: 2015-03-26
• [Presentation] メディシナルフラワー研究: キンモクセイ (Osmanthus fragrans var. aurantiacus) 花部の含有成分 (2014)
  • Author(s): 太田智絵, 深谷 匡, 中村誠宏, 劉 江, 許 斌, 吉川雅之, 松田久司
  • Organizer: 第64回日本薬学会近畿支部総会・大会
  • Place of Presentation: 京都府京都市 京都薬科大学
  • Year and Date: 2014-10-11
• [Presentation] タイ産イランイランノキ (Cananga odorata) 花部の生体機能性成分 (2014)
  • Author(s): 松本崇宏, 安井理絵, 中村誠宏, 中嶋聡一, 吉川雅之, 松田久司
  • Organizer: 第64回日本薬学会近畿支部総会・大会
  • Place of Presentation: 京都府京都市 京都薬科大学
  • Year and Date: 2014-10-11
• [Presentation] インド産アッサム種茶花 (Camellia sinensis var. assamica) の新規トリテルペン配糖体成分 (2014)
  • Author(s): 太田智絵, 中村誠宏, 松本崇宏, 吉川雅之, 小川慶子, 深谷 匡, 松田久司
  • Organizer: 第58回香料・テルペンおよび精油化学に関する討論会
  • Place of Presentation: 和歌山県和歌山市 和歌山大学
  • Year and Date: 2014-09-21
• [Presentation] メディシナルフラワー研究: キンモクセイ花部の抗炎症作用成分 (2014)
  • Author(s): 許 斌, 中村誠宏, 劉 江, 王 巍程, 深谷 匡, 吉川雅之, 松田久司
  • Organizer: 日本生薬学会第61回年会
  • Place of Presentation: 福岡県福岡市 福岡大学
  • Year and Date: 2014-09-14
• [Presentation] メディシナルフラワー研究: 中国産白梅花の新規生体機能成分 (2014)
  • Author(s): 中村誠宏, 太田智絵, 藤本勝好, 中嶋聡一, 松本崇宏, 吉川雅之, 宮下 優, 深谷 匡, 柏崎絵李, 松田久司
  • Organizer: 日本生薬学会第61回年会
  • Place of Presentation: 福岡県福岡市 福岡大学
  • Year and Date: 2014-09-14
• [Remarks] 京都薬科大学 教育・研究 教員／研究室・附属施設一覧 創薬科学系 - 生薬学分野
  • URL: https://www.kyoto-phu.ac.jp/education_research/laboratory/?c=laboratory_view&pk=4
• [Remarks] 京都薬科大学 教育・研究 研究室・附属施設の紹介 生薬学分野
  • URL: http://www.kyoto-phu.ac.jp/education_research/laboratory/cat/post_10.html